# US 11,439,589 B2 · Emulsion eyedrops

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- Number: US 11,439,589 B2
- Document ID: US11439589B2
- Status: Granted
- Kind: B2
- Application number: 16/348,538
- Filed: 2017-11-16
- Published: 2020-02-20
- Granted: 2022-09-13
- Earliest claimed: 2016-11-17
- Assignees: Senju Pharmaceutical Co., Ltd.
- Applicants: Senju Pharmaceutical Co., Ltd.
- Inventors: Yasuhiro Mori
- Web page: https://patentgrep.com/patent/US11439589B2

## CPC

- A61K 9/0048: {Eye, e.g. artificial tears}
- A61K 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)}
- A61K 31/405: Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A61K 31/57: substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K 47/32: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone}
- A61K 47/44: Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin (synthetic glycerides, e.g. medium-chain triglycerides, A61K47/14)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

Provided are: emulsion eyedrops which have no concern with possible corneal injury induced by a nonionic surfactant, have excellent thermal stability and physical stability and can contain a sparingly water-soluble drug in an increased amount; and an emulsion eyedrops stabilization method. The emulsion eyedrops contain castor oil and poly(vinyl alcohol), wherein the concentration of castor oil is 5 to 20 w/v %, the concentration of poly(vinyl alcohol) is 2 to 7 w/v %, and the ratio of the weight of castor oil to the weight of poly(vinyl alcohol) is 1.2 to 5. The emulsion eyedrops stabilization method is characterized by preparing emulsion eyedrops containing castor oil and poly(vinyl alcohol), wherein the concentration of castor oil is 5 to 20 w/v %, the concentration of poly(vinyl alcohol) is 2 to 7 w/v %, and the ratio of the weight of castor oil to the weight of poly(vinyl alcohol) is 1.2 to 5.

## Claims

### Claim 1

Emulsion eyedrops comprising castor oil and poly(vinyl alcohol), wherein the concentration of the castor oil is 5 to 20 w/v %, the concentration of the poly(vinyl alcohol) is 2 to 7 w/v %, the ratio of the weight of the castor oil to the weight of the poly(vinyl alcohol) is 1.2 to 5,
wherein no nonionic surfactant is present,
wherein the average particle diameter of oil droplets contained in the emulsion eyedrops before the sterilization in the autoclave is 100 to 200 nm,
wherein the emulsion eyedrops do not contain water-soluble polymers other than poly(vinyl alcohol),
and wherein, when the emulsion eyedrops are sterilized in an autoclave at 121° C. for 20 minutes, the rate of change in the average particle diameter of oil droplets contained in the emulsion eyedrops before and after the sterilization in the autoclave is less than 3%.

### Claim 2 (depends on 1)

The emulsion eyedrops according to claim 1, wherein a sparingly water-soluble drug is further contained.

### Claim 3 (depends on 1)

The emulsion eyedrops according to claim 1, wherein, when the emulsion eyedrops are centrifuged at 20000×g for 20 minutes, the emulsion eyedrops are homogeneous.

### Claim 4

An emulsion eyedrops stabilization method, comprising the step of preparing emulsion eyedrops containing castor oil and poly(vinyl alcohol), wherein:
the concentration of the castor oil is 5 to 20 w/v %;
the concentration of the poly(vinyl alcohol) is 2 to 7 w/v %; and
the ratio of the weight of the castor oil to the weight of the poly(vinyl alcohol) is 1.2 to 5, wherein no nonionic surfactant is present, wherein the average particle diameter of oil droplets contained in the emulsion eyedrops before the sterilization in the autoclave is 100 to 200 nm, wherein the emulsion eyedrops do not contain water-soluble polymers other than poly(vinyl alcohol), and wherein, when the emulsion eyedrops are sterilized in an autoclave at 121° C. for 20 minutes, the rate of change in the average particle diameter of oil droplets contained in the emulsion eyedrops before and after the sterilization in the autoclave is less than 3%.

### Claim 5 (depends on 4)

The stabilization method according to claim 4, wherein the emulsion eyedrops further contain a sparingly water-soluble drug.

### Claim 6 (depends on 4)

The stabilization method according to claim 4, wherein, when the emulsion eyedrops are centrifuged at 20000×g for 20 minutes, the emulsion eyedrops are homogeneous.